1,2-Dibromoethane → 1-(3-Chloro-2-methylphenyl)cyclohexanol

HRID 249462

反応式

HRID 249462 の反応式
BrCCBr.Cl[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[CH3:13].[C:14]1(=[O:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>O1CCCC1>[Cl:12][C:8]1[C:7]([CH3:13])=[C:6]([C:14]2([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:11]=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 78391,2-DibromoethaneHCID 7967CyclohexanoneHCID 83682,6-Dichlorotoluene

生成物 1

HCID 145554331-(3-Chloro-2-methylphenyl)cyclohexanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

96 g (4 moles) of Mg turnings in 60 ml of absolute tetrahydrofuran (THF) are initially taken under a nitrogen atmosphere. 1 ml of 1,2-dibromoethane is added at 65° C., after which a solution of 644 g (4 moles) of 2,6-dichlorotoluene in 1.5 1 of absolute THF is added dropwise in the course of 21/4 hours. Thereafter, the mixture is stirred for 4 hours under reflux and cooled to room temperature, and 352.8 g (3.6 moles) of cyclohexanone in 250 ml of absolute THF are added under nitrogen. When the reaction is complete, the Grignard reaction mixture is worked up in an aqueous medium in a conventional manner and the solvent is substantially removed by distillation under reduced pressure. The residue is subjected to incipient distillation (30°-107° C./0.27 mbar). The remaining crude product (676 g), which contains as much as 90% of 1-(3'-chloro-2'-methylphenyl)-cyclohexanol, can be further purified by column chromatography using toluene as the mobile phase.

後処理

  1. temperatureunder reflux
  2. customthe Grignard reaction mixture
  3. customthe solvent is substantially removed by distillation under reduced pressure
  4. distillationThe residue is subjected to incipient distillation (30°-107° C./0.27 mbar)
  5. customcan be further purified by column chromatography

出典と根拠

ORDレコード
ord-b33c2528f031498c8ad5385a6c7670fc
出典データセット
uspto-grants-1993_05
特許番号
US05214187

関連ノート

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